


Lily's Journal

by Charlie_E_Winchester



Series: Stories From The Bunker [4]
Category: Supernatural
Genre: F/M, Mild Smut
Language: English
Status: In-Progress
Published: 2015-12-19
Updated: 2015-12-19
Packaged: 2018-05-07 15:23:21
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,246
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5461352
Author URL: https://archiveofourown.org/users/Charlie_E_Winchester/pseuds/Charlie_E_Winchester
Summary: <blockquote class="userstuff">
              <p>Before retirement, before Destiel, before the end of the war, Dean must deal with the loss of one of his oldest friends.</p>
            </blockquote>





	1. Prologue

Dean looked down at the limp body in his arms, crying softly. She'd been such a rare constant in his life - something he'd never questioned - that he hadn't considered one day she might not be there anymore. 

But here she was, dead like all the rest. Gone to join Bobby, Jo, Ellen, Benny, Kevin, Charlie... the list continued on so long that Dean started weeping openly just thinking about it. He should have known better than to keep up with her all these years. He should have known something like this would happen to her, simply as a by-product of her association with Dean Winchester. Even if he'd never told anyone about her. Even if he thought she'd been his secret. 

He lay her down gently on her bed. Her eyes were closed and her mouth parted slightly. She looked like she could just be sleeping peacefully. He knelt next to the bed, put his hands together, and prayed. Not for himself, but for her. She'd always prayed before bed. Every night. She, unlike Dean, still trusted God. But Dean knew how much it would mean to her to have a final prayer said in her name. So he closed his eyes and did his best to do her justice.

_God, listen, I know you hear a lot from me, but this one isn't for me, okay? This is for her. She always liked to talk to you. And I hope you know she didn't deserve this. I hope you know she was a good person - even if she did get mixed up with me - and she deserves what you do for good people. Please, God, if you're listening, take care of her up there._

Dean opened his eyes and brought her hands to his lips one last time. He held them there, the tears still streaming down his cheeks. 

Cas strode into the room abruptly. 'Dean, we need to leave. It won't be long until they realize the demon who possessed her no longer exists.' 

Dean looked up at his friend, placing Lily's hands gently back down. 'Okay Cas.' His voice broke. 'I just needed a minute.' 

Cas nodded, his look softening. 'I am sorry Dean. Were you two close?' 

Dean wiped the tears from his eyes, nodding roughly. 'Yeah, you could say that. We'd known each other a long time.' 

'Is there anything of hers you'd like to bring with us?' Cas' eyes swept the room. 'A memento of your friendship?' 

Dean shrugged, his hand still wrapped around hers and resting gently on her chest. He began to look around the room. 'I'd like her journal. She always wrote in a journal.' He sighed deeply. 'She was really a beautiful writer.' 

Cas nodded in understanding, and together they searched the room until they found a large, leather-bound journal filled with flowing cursive words. Dean grasped it firmly as he left the house in a hurry. He fought the urge to look back at her one last time. 

As he sat behind the wheel of the Impala, putting her house and his life with her in the taillights, Dean sighed heavily again. He was running out of friends to lose to this life. 

Cas sat next to him, slowly flipping through the heavy pages of the journal. "She really does have beautiful handwriting," he murmured. He turned his face to Dean. "May I read it?" 

Dean shrugged. He couldn't think of anything that would be in there that Cas wouldn't have seen in the years he watched over Dean. 

With a small smile of delight, Cas turned back to the first page of the journal and buried his face in it. Dean stared silently at the road ahead, his mind likely reliving much of what was written in the journal. 


	2. July 10, 2003

**Summary for the Chapter:**

> _I think I just had the best night of my life._

Oh. My. God. I don't even know if what happened was real. It seems like something that happens in movies, or in those romance novels you read to keep you warm at night. 

I met a man. A man I'll probably never see again, to be honest. But hot damn was that man worth it. 

I was working the bartending shift last night, and he plops himself down in one of the barfly seats at about 10pm. Orders himself a shot of jack and a beer. Such a dude order. 

At first I thought he looked a little rough around the edges, but he was all polite when I brought him his drink, asked my name, and smiled at me when I told him. I will hear those words in my heads for weeks. 

'Lily. Beautiful flowers. Beautiful name,' he tipped his beer at me, 'for a beautiful woman.' 

Oh god, that smile! It could melt your heart clear out of your chest. Or light a fire inside you. Maybe both. 

So he keeps smiling at me and keeps calling me by name all night. He seems to enjoy saying my name. I like hearing it roll of his tongue. He tells me he's just passing through, on his way to check up on his baby brother whose in college. He didn't seem bothered that it's the summer semester \- says his brother stays out there to work as a TA or something. Must be a smart kid. His eyes really lit up when he talked about his brother. It was that that really told me he wasn't just another one of the truckers passing through. This guy had a heart of gold hidden behind that drinking problem. 

Towards the end of the night, he's getting even chattier. It's slow, and I can stay and talk with him while my regulars stare into their drinks. Nobody in that bar has ever talked to me the way he does. And before I know it, he's asking for two shots with his next round. Wants me to take the other one. 

And I know the bar has a policy - if the customer keeps paying, and giving you shots makes them happy, you keep 'em happy - but I do my best to stay away from guys who want to watch me drink. I usually tell them I'm driving, that I'm already on the cusp of drunk, whatever works. But, I don't know what made me change my mind; this guy was a smooth talker. 

So there I am, leaning over the bar talking to him, and now I'm pouring the two of us shots. I have no idea what came over me. I usually pride myself in being above all that flirty-ness, but _god_ did this man know how to work me. I was showing off as best I could, hoping that he liked it. He certainly liked watching me take the shots. He smiled as my head tilted back, each time. I think to him it was a special kind of foreplay. 

He ends up being my last customer at the bar. I kicked the rest of them out, same as usual, but he's fumbling for his credit card and making a big show of 'almost' leaving. As soon as the last guy is out the door, he's giving me the eye. He wants a night cap before I close up the joint. 

And of course, we've been drinking enough shots at this point that I'm a little tipsy. I know I'm going to have to leave my car there now. So I ask him if he wants to just get his night cap at my place. I tell him he needs to do the gentlemanly thing and walk me home, since it's _his_ fault I can't drive anymore. 

As soon as I say it, he gets this big grin on his face. It's adorable and sexy at the same time. 

When I get the bar door locked behind us, he's there. He kisses me so deeply I can feel his breath at the back of my throat. I can't help it - I melt into him. His hands are already up my shirt, on my back and tracing along my skin. Even just that feeling causes me to moan. 

Before I know it he's not kissing me anymore. He's down in front of me on his knees, fingers rolling up my skirt and pulling aside the little black lace thong I like to wear on Friday nights. He's grinning impishly up at me before starting to explore me, first with his fingers and then lightly with his tongue. 

I couldn't believe I was letting him do it. In the back alley behind the bar, up against a wall, where literally anyone could have walked past us. It was terrifying and _so exciting._ I ran my fingers through his soft hair as he started to really explore me. I did my best to moan softly so no one could hear. 

He was an expert. His tongue made just the right pressures, his fingers spreading me wider so he could press deeper, and lick me just a little harder. He massaged around my lips before slowly sliding a finger inside me, then back out quickly to massage again. As I started to twitch, feeling the pleasure of climax coming closer, he seemed to sense it. He slipped two fingers inside, pulsing them in and out of me, all while his tongue danced figures around my swollen mound. 

I couldn't help it. When the orgasm came I moaned, softly but deeply. Lord, I didn't orgasm like _that_ normally. It seemed to rock through my whole body like waves, crashing one on top of the other. Some people say an orgasm is like a sneeze. Well this man was showing me that _that_ kind of an orgasm was only child's play compared to what he could do to me. 

And suddenly he was back up in front of me, slickly sliding my skirt back down and nibbling along my neck. He had a shit-eating grin on his face. He took my hand and pulled me around the corner, leading me back into the light of the main street. I could barely walk I was still tingling so much.  

Going into my house with him was like entering a place I'd always known but never truly experienced. He led me by the hand to the bedroom and kissed me deeply. But this time he was gentle; he wanted to be led to what I wanted from him. And our rendez-vous at the bar had me so excited I was ready to pounce on him. 

I pushed him against the wall and kissed him, starting with his lips, working my way down his chin and to his neck. I reached one hand down to stroke his growing bulge. I loved hearing the little gasp of breath he let out. 

Honestly, I'm not the leading type in the bedroom. But something about him brought it out in me. 

Before I knew it, his shirt was tossed aside and I was kissing down his chiseled chest. This man had a beautiful face, but his body was like icing on the cake. As my kisses ventured lower, I quickly ripped his belt open and slid his pants down to his ankles. He was ready to explode from his boxers, practically pulsing in front of me. 

When I took him into my mouth, I loved hearing his moan above me. I wrapped one hand around him and began to stroke up and down in time with the motion of my mouth, flicking his tip with each rise to the top. Lord, I loved that I made him shiver with pleasure. 

His fingers ran through my hair, one hand placed against the wall behind him for support. I felt him grow closer to climax and pulled my head away. From my place between his legs I looked up at him, grinning devilishly. 

'You need to go to bed,' I commanded. 

I stood up in front of him and pointed to my bed. He pouted playfully at me, and I put my hands on my hips. 

'If you want to keep playing, you have to go to bed.' 

He grinned impishly at me again, kicking his pants out from under his ankles and springing for my bed. He bounced on it like a happy child and turned up at me. 

'I'm here,' he said, 'what are you going to do to me?' 

I slowly undressed in front of him, taking care to keep my eyes on him as I did it. 'I'm going to do whatever I want to do to you,' I said. I couldn't believe I was taking charge like that. 

I don't think we slept that night. If we did, it was only briefly. When we were finally both at the peak of being unable to experience more pleasure from each other, we lay next to each other quietly, catching our breaths. A thought occurred to me and I rolled off the bed slowly, coming to my knees and putting my hands, firmly clasped together, on top of the mattress. 

He looked over at me, a quizzical look on his face. 'Did I just make you come so hard you have to commune with God?' he laughed. 

I opened one eye and did my best to playfully glare at him. 'I always pray to God. Every night. Just because there's a naked man in my bed doesn't change that.' 

He shrugged and lay his head down on the pillow. I expected him to roll over, ignore me as the other men in my life had done. Instead, he watched me. There was no look of judgment on his face; just a look of peaceful curiosity. 

I closed my eyes and talked to God. I knew I didn't have to pray out loud - that was just a thing movies liked to do so they didn't have to use voiceovers . 

When I crawled back into bed, he ran his fingers gently through my hair, his curious look so innocent. He really wasn't like other men I'd had in my bed. 

'Did you ask him forgiveness for the things we've just done?' 

I laughed. 'No. I don't think God cares what two consenting adults do with each other. He designed our bodies to feel pleasure; I'd like to believe he enjoys that we explore our options.' 

'Do you think he listens?' 

I looked over at this strange man I'd just met; he had just asked me a very serious question. A question many people who decide whether they are going to have faith in their lives have to ask themselves. And he didn't ask it mockingly, or judgingly, or as if he'd found a different answer to the question himself. He seemed to ask because he'd never considered the question himself. 

I nodded, slowly, looking away from him and up at the ceiling. 'I think even when he can't help he listens. I don't think God is supposed to fix everything, but I do think he's like an old friend; when he's too far away to help you, sometimes all he needs to do is listen so you can figure out how you can help yourself.' I looked back at him, smiling. 'So I always talk to God like he's an old friend.' 

He nodded, moving forward to lay his head on my shoulder. it was slowly growing light outside, and he looked out the window. 'I'm going to have to go soon.' 

'I know. I know the drill. You're just passing through.' 

He chuckled. 'I take it I am not your first bar fly.' 

I placed my finger on his nose, eliciting a smile. 'Let's not pretend I'm your first bartender.' 

He kept smiling as he lifted his head up to look at me. 'Would it be alright, you know, if I came to see you again sometime?' 

I shrugged, doing my best to seem casual, even though the thought of getting to experience this man again excited me beyond measure. 'Only if you tell me your name.' 

He lay his head back town, curving his whole body to lay slightly over mine. 'Dean.' he said slowly. 'My name is Dean Winchester.' 

I must have fallen asleep as we lay there, because when I opened my eyes he was gone. 


	3. January 25, 2004

**Summary for the Chapter:**

> _Well Diary, I don't think you'll believe who popped back into my life yesterday_

I was working the dinner shift at the bar again, when none other than the infamous Dean Winchester showed his face. He just walked in and plopped himself down on the same bar stool he'd been sitting on six months ago. Even though he asked me if he could come back, I never honestly expected to see him again. 

He fixed me with a small smile when he saw I was the one working, lifted his eyebrow and just asked for 'the usual.' Something in this man brings out the adventurous girl in me. I poured his beer, and two shots of Jack. He seemed confused until he realized I intended to take the second one. At that point, he gave me such a wicked grin - damnit if it couldn't melt your heart and make you wet at the same time - and tipped his drink to me. 

At first it was all going the same as before - he bought me shots and I did my best to be flirty without ignoring my other customers _too_ much. I was just closing out my sales when it seemed like shit hit the fan. The doors to the bar slammed open loudly, and in storm a bunch of guys looking _pissed_. I knew most of them from around town, but they'd never caused trouble in the bar before. I couldn't understand why they were suddenly barging through doors like they wanted to burn the place down. 

Just as I'm sizing these guys up, I steal a glance at Dean in front of me. He raises his eyebrows at me, whispers "Well, shit" and takes his last shot. I don't know why I remember that moment so distinctly, but I do. Something about that moment hit me. I put my hand on his, trying to impart on him the need for him to stay in his seat. 

I walked around the bar to the group of guys and did my best to appear tall; not an easy feat since I'm only 5' 6". I stood firm and raised my head to the man in the centre of the pack. He seemed to be the most pissed out of any of them. "What's the problem, Doug?" 

Doug pointed a finger at Dean, still sitting at the bar. "I'll tell you what the problem is Lily. That fucker over there owes us money." He looked down his nose at me. "That money he's been drinking off of here is mine; he cheated at the pool hall. Jackoff swindled us." 

I raised my eyebrow. "Oh, is _that_ where he was before?" I gestured behind me at Dean, but was careful not to look at him. "I was wondering what bar he wandered in from, since he came in here sloshed off his ass. I couldn't believe someone over-served him that much." I raised an eyebrow at Doug. "Your sister's still the bartender at the pool hall, right?"

He scowled at me, but he seemed to get the hint. "He still owes me money," he growled.  

I did my best to chuckle, tapping Doug playfully on the arm. "Doug, sweetie, considering how drunk he was when he came in here, you probably deserved to lose that money." 

I looked around at the rest of them. "Now if you'll excuse me boys, unlike some bartenders -" I threw my best dirty look at Doug, "- I'm going to make sure this poor guy gets into a cab, so he can go home and sleep it off." I grabbed my jacket from behind the bar, took Dean by the arm, and marched him out of the bar. 

As soon as we were around the corner I felt all my confidence wither. My hands started shaking, and I had to stop to take a few breaths of the cold winter air to steady myself. 

Dean wrapped his hands around mine and kissed me. "Well that was one hell of a show." 

I chuckled. "Can't have you getting beat up in my bar." I kissed him back. "Bad for business." 

Dean kissed me again, smiling the whole time. Keeping my hands in his, he led me back to his car - this gorgeous old Impala - and offered to drive me home. As we were driving, I commented on the excellent shape his car was in. 

He grinned sheepishly. I seemed to have struck a point of pride for him. "Yeah, I help take care of it, but it's actually my Dad's. He wanted something a little more subtle for the job he's on, so he let me borrow it." 

"Are you going to visit your brother again?" 

Dean shook his head. "Nope, just driving around while Dad's working. I was in the area and was hoping maybe you were still around." 

I laughed. "Trust me, I'm not going anywhere. Born and raised here. I'll probably die here." 

This seemed to silence him. Finally, Dean glanced over at me. "You know I did take those guys for all they were worth, right? He wasn't lying." 

I smiled to myself. "I figured. But Doug's an idiot; he deserves to get shown that every now and again." 

This time it was Dean's turn to laugh. I really loved his laugh; it sounded so full and honest. 

When we got back to my place, I showed him the fake stone where I hid my emergency key. "For next time, so you don't have to wait for me at the bar." 

Dean grinned, turning me around and kissing me deeply while my back was still pressed against the front door. "Is this you inviting me to come back?" 

I brought my finger up to wag in his face. "Third date means dinner. That means if you come back, I expect a home cooked meal waiting for me in this kitchen." 

He kissed me again, opening the door behind us and causing us to tumble in, still kissing and slowly caressing our hands over each other. We literally left a trail of clothes behind us as we ventured to the bedroom - oh diary, how cliché of me! - and before my brain could register what my body was leading it to, he was on top of me. 

This time was so different from the last - he was very much the one in charge. He held my hands above my head, thrusting deeply and rhythmically into me. His hips seemed to tilt up just at the peak of impact, sending ripples of pleasure through me. 

When we were finished, panting and sweaty, he seemed different. He didn't say anything to me as he rose to the bathroom, and it was only after I heard the loud sound of the water that I realized he'd decided to shower. I took the time to kneel beside the bed, closing my eyes and praying quietly. 

I opened my eyes to see him standing in the doorway, his hair ruffled and a towel wrapped around his waist. "Sorry, I just," he raised him arms helplessly by  his side. "I'm not usually like that." His voice got lower. "I didn't want to be like that with you." 

I rose from the bed and took his hands in mine, guiding him back to the edge of the bed. "You're allowed to be however you want with me, Dean. I don't mind a guy who likes to make things a little rough in bed." I fought for his gaze, and held it when I found it. "Listen, if I am not okay with something you are doing, I am going to tell you." 

I took my hand and began to unwrap the towel around his waist. "And I'd like you to extend me the same courtesy. If I'm doing something you don't like, you just have to tell me." I got to my knees in front of him, gently stroking him. "You just have to tell me to stop, if that's what you want." I slid my lips slowly over his tip, throwing my eyes up at him. Just like I thought; he was watching; he seemed like the type who liked to watch. I began moving my lips up and down, flicking him gently with my tongue as I went. 

He let out a low moan and I took this as my cue. I brought one hand up to massage between his thighs. I carefully took one, then both, of his balls in my hand, tugging gently as I increased the speed of my lips. His moan took the form of words at one point - "Oh god, don't stop" - which seemed fitting in the moment. As he came, he rocked forward and I went with him, keeping my mouth wrapped around him and pulling gently to entice the last twitches of pleasure out of him. 

I pushed him back on the bed and continued to lightly run my lips along him. Gently. I wasn't disappointed; I was able to elicit another great shudder from him. 

He curled up next to me in bed that night, but I still woke up by myself. He left me a note this time. 

' Thanks for the best birthday I've had in a long time 

I suppose that's Dean Winchester for you, diary. 


End file.
